219932-11-3

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 67-56-1 methanol 

Downstream Products

• 316790-20-2 (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane 
• 1258388-22-5 (Z)-(4R,5R)-1-n-octylamino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one 
• 1258388-24-7 (E)-(4R,5R)-1-diethylamino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one 
• 1258388-21-4 (Z)-(4R,5R)-1-n-butylamino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one 
• 1258388-23-6 (Z)-(4R,5R)-1-anilino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one 
• 1258388-20-3 (Z)-(4R,5R)-1-benzylamino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one 
• 1125483-09-1 (2R,3S,4R)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 

Relevant academic research and scientific papers

Macrolide Core Synthesis of Calysolin IX Using an Intramolecular Glycosylation Approach

The utility of intramolecular glycosylation for the synthesis of the 27-membered macrocyclic ring is highlighted in this first total synthesis of the most complex resin glycoside isolated to date – Calysolin IX. Oligosaccharide-containing macrolides core

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).

Electrochemical Trifluoromethylation of Glycals

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals b

Guidelines for β-lactam synthesis: Glycal protecting groups dictate stereoelectronics and [2+2] cycloaddition kinetics

The alkene-isocyanate cycloaddition method affords β- lactams from glycals with high regio- and stereoselectivity, but the factors that determine substrate reactivity are poorly understood. Thus, we synthesized a library of 17 electron-rich alkenes (glyca

Synthesis of O-1- O-6 Substituted Positional Isomers of d -Glucose-Thioether Ligands and Their Ruthenium Polypyridyl Conjugates

A library of positional isomers of d-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.

P-chlorobenzyl ether: A p-methoxybenzyl ether in disguise

In the chemistry of polyfunctionalized organic compounds, protecting groups that can undergo mild and selective cleavage while still being stable during the entire synthetic sequence are often required. In this work, we present a straightforward conversion of the robust p-chlorobenzyl ether into the more labile and well-described p-methoxybenzyl ether using palladium catalysis. This reaction was demonstrated to be high yielding and compatible with a wide range of functionalities, thereby providing a useful supplement to the conventional ether protecting groups.

Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis

A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.

Discovery of carbohybrid-based 2-aminopyrimidine analogues as a new class of rapid-acting antimalarial agents using image-based cytological profiling assay

New antimalarial agents that exhibit multistage activities against drug-resistant strains of malaria parasites represent good starting points for developing next-generation antimalarial therapies. To facilitate the progression of such agents into the development phase, we developed an image-based parasitological screening method for defining drug effects on different asexual life cycle stages of Plasmodium falciparum. High-throughput screening of a newly assembled diversity-oriented synthetic library using this approach led to the identification of carbohybrid-based 2-aminopyrimidine compounds with fast-acting growth inhibitory activities against three laboratory strains of multidrug-resistant P. falciparum. Our structure-activity relationship study led to the identification of two derivatives (8aA and 11aA) as the most promising antimalarial candidates (mean EC50of 0.130 and 0.096 μM against all three P. falciparum strains, selectivity indices >600, microsomal stabilities >80%, and mouse malaria ED50values of 0.32 and 0.12 mg/kg/day, respectively), targeting all major blood stages of multidrug-resistant P. falciparum parasites.

Preparation and reactivity of imino glycals: Stereocontrolled, divergent approach to imino sugars

The synthesis of 3,4,6-tri-O-acetyl imino D-glucal 2 from D-glucal is reported. This imino glycal participates in a variety of Lewis acid mediated carbon-carbon bond forming reactions by allylic displacement of the C-3 acetate group by added nucleophiles. Allyl silanes, trimethylsilyl enol ethers, alkenes and dialkyl zinc reagents serve as suitable reaction partners. In all the cases studied, the (3-anomer is predominant. Using imino glycal 8, epimeric at C-5, it is established that the configuration at C-5 of the piperidine ring plays a major role in controlling the stereochemical outcome. These results are rationalised by invoking the intermediacy of a conjugated W-acyliminium ion. A short stereocontrolled synthesis of (+)-deoxoprosophylline is achieved using this chemistry. Additionally, imino glucal 2 is transformed into bromo piperidine 16, whose X-ray crystal structure is determined. Bromide 16 participates in palladium catalysed Stille and Suzuki cross-couplings allowing access to C-2 substituted imino sugars 17 and 18. In other studies, imino sugar C-glycosides 21 and 22 are made by combining the Lewis acid mediated carbon-carbon bond forming reactions with stereospecific dihydroxylations.

Synthesis of some biologically relevant β-C-glycoconjugates

(Matrix presented) An esterification-RCM approach to a variety of biologically relevant β-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then con